Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.1K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
5.1K
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.1K
Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
2.1K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

2.9K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
2.9K
Radical Formation: Addition00:47

Radical Formation: Addition

1.7K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
1.7K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.0K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.0K
Radical Formation: Overview01:03

Radical Formation: Overview

2.1K
A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the...
2.1K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Publisher Correction: Surviving Sepsis Campaign: international guidelines for management of sepsis and septic shock 2026.

Intensive care medicine·2026
Same author

Cu<sub>7.62</sub>Bi<sub>6</sub>Se<sub>12</sub>Cl<sub>6</sub>I: Discovery of a Low Band Gap, Low Thermal Conductivity Mixed-Anion Material.

Chemistry of materials : a publication of the American Chemical Society·2026
Same author

Clinical Criteria for the Definition of Refractory Septic Shock: A Joint Delphi Consensus from the Society of Critical Care Medicine (SCCM) and European Society of Intensive Care Medicine (ESICM).

Critical care medicine·2026
Same author

Clinical criteria for the definition of refractory septic shock: a joint Delphi consensus from the Society of Critical Care Medicine (SCCM) and European Society of Intensive Care Medicine (ESICM).

Intensive care medicine·2026
Same author

Executive Summary: Surviving Sepsis Campaign: International Guidelines for Management of Sepsis and Septic Shock 2026.

Critical care medicine·2026
Same author

Surviving Sepsis Campaign: International Guidelines for Management of Sepsis and Septic Shock 2026.

Critical care medicine·2026
Same journal

Catalytic synthesis of saturated azacycles using transborylation.

Organic & biomolecular chemistry·2026
Same journal

Pyridines with adamantane fragments and their 1,2,4-triazine analogues as anti-quorum-sensing agents, synthesis and molecular docking.

Organic & biomolecular chemistry·2026
Same journal

Synthesis of polymethylene-linked bis(cyclobutane-fused chromanones) mediated by gold photocatalysis.

Organic & biomolecular chemistry·2026
Same journal

Palladium-catalyzed chelation-assisted C-H functionalization of quinoline aldehydes to esters with mechanistic insights.

Organic & biomolecular chemistry·2026
Same journal

One-pot metal-free access to uracil-benzofuran bis-heterocycles: synthesis and DFT insights.

Organic & biomolecular chemistry·2026
Same journal

Transition-metal-free three-component synthesis of α-tertiary trifluoromethyl phosphonates from CF<sub>3</sub> diazo compounds.

Organic & biomolecular chemistry·2026
See all related articles

Related Experiment Video

Updated: Jul 6, 2025

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
14:22

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development

Published on: April 15, 2013

20.3K

An assay for aryl radicals using BHAS coupling.

Kenneth F Clark1, Seb Tyerman1, Laura Evans2

  • 1Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK. john.murphy@strath.ac.uk.

Organic & Biomolecular Chemistry
|January 10, 2024
PubMed
Summary
This summary is machine-generated.

This study quantifies a base-induced homolytic aromatic substitution reaction. The findings reveal a distinct deuterium isotope effect, establishing this reaction as a sensitive assay for detecting aryl radicals.

More Related Videos

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

2.8K
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

25.4K

Related Experiment Videos

Last Updated: Jul 6, 2025

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
14:22

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development

Published on: April 15, 2013

20.3K
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

2.8K
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

25.4K

Area of Science:

  • Organic Chemistry
  • Reaction Mechanisms
  • Radical Chemistry

Background:

  • Aryl radicals are crucial reaction intermediates but difficult to detect.
  • Base-induced homolytic aromatic substitution (BHAS) offers a potential pathway for aryl radical generation and reaction.

Purpose of the Study:

  • To quantitatively investigate a BHAS coupling reaction involving 2-iodo-1,3-dimethylbenzene.
  • To explore the mechanistic details and potential of this reaction as an aryl radical assay.

Main Methods:

  • Quantitative analysis of coupling products (biphenyl and dimethylbiphenyl).
  • Deuterium isotope effect studies using C6D6 versus C6H6.
  • Investigation using various radical initiation sources.

Main Results:

  • The reaction consistently produced biphenyl and 2,6-dimethylbiphenyl in a ratio of approximately 4:1.
  • A significant deuterium isotope effect was observed for biphenyl formation but not for dimethylbiphenyl.
  • The BHAS process demonstrated high sensitivity due to its chain reaction amplification of radical activity.

Conclusions:

  • The observed deuterium isotope effect provides strong mechanistic evidence for aryl radical involvement.
  • The BHAS transformation serves as a reliable and sensitive assay for detecting aryl radicals.
  • This method offers an advantage due to the inherent sensitivity of the chain reaction.